Could you please explain some of the terminology that is commonly used for carbonyl chemistry – alpha beta, and especially 1,4. And provide suggestions on keeping things sorted in memory. Or provide a link if you have already done so.

The numbering particularly threw me when I was a student. We had just become comfortable numbering carbons for nomenclature and here comes carbonyl chemistry to derail us.

Great question. It has to do with a topic that doesn’t get much discussion in organic chemistry until later on – called “Hard-soft acid-base theory”. Nucleophiles with a concentrated charge density like organolithiums and Grignards tend to add to the atom of the enone with the highest charge density (the carbonyl carbon). For a full explanation I’d need to invoke molecular orbital theory.

With morpholine, only the nitrogen will be nucleophilic in that case. The oxygen would lead to a positively charged species that cannot become neutral through loss of hydrogen. If you had to compare a molecule with an amine and an alcohol, say, ethanolamine, the nitrogen would be more nucleophilic since nucleophilicity of a lone pair increases as you go to the left along the periodic table (N > O)